083: How Cassi Transitioned out of the Classroom and into EdTech Corporate

083: How Cassi Transitioned out of the Classroom and into EdTech Corporate

From Pretty Rich Teacher by Dr. Jazmyne Dionne

May 29, 2026 · 41 min

About this episode

Cassi shares her journey of leaving a 15-year teaching career for a role in EdTech, discussing the challenges and fears faced during the transition.

Fifteen years in the classroom. And one day, it just wasn't enough anymore. In Episode 83, Jazmyne sits down with Cassi, a former elementary educator who walked away from a 15-year teaching career and landed an EdTech corporate role. Not because it was easy. Because she stopped waiting for permission to want more. This isn't a feel-good story about following your passion. It's a real conversation about the fears that keep teachers stuck — retirement, benefits, identity, feeling "not qualified enough" — and what it actually takes to move through them. Jazmyne and Cassi breaks down: Why teachers struggle in corporate interviews (and how she fixed it) How she stopped selling herself as a teacher and started positioning as a professional What life actually looks like without the Sunday scaries, the late-night lesson plans, and the emotional weight she didn't realize she was carrying If you've been quietly thinking "I can't do this forever", then this episode is your answer. Are you a burnt out women in education looking to leave the classroom but don't know where to start? Click here for our podcast listening guide filled with 50+ hours of free training Ready for 1:1 mentorship, a…

People in this episode

Host: Dr. Jazmyne Dionne

Guest: Cassi

Topics covered

  • career transition
  • EdTech
  • teacher burnout
  • corporate interviews
  • professional identity

Keywords

  • teacher transition
  • EdTech career
  • corporate roles
  • teacher struggles
  • professional development

Mentioned in this episode

Organizations: EdTech

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